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Ferrocenyl-Imidazolylidene Ligand for Redox-Switchable Gold-Based Catalysis. A Detailed Study on the Redox-Switching Abilities of the Ligand

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    Ferrocenyl-Imidazolylidene Ligand for Redox-Switchable Gold-Based Catalysis. A Detailed Study on the Redox-Switching Abilities of the Ligand
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    † Instituto de Materiales Avanzados (INAM), Universitat Jaume I, Avenida Vicente Sos Baynat, 12071 Castellón, Spain
    ‡ Department of Chemistry and Biochemistry, Wilfrid Laurier University, Waterloo, Ontario N2L 3C5, Canada
    *E-mail (M. Poyatos): [email protected]
    *E-mail (E. Peris): [email protected]
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    Organometallics

    Cite this: Organometallics 2016, 35, 16, 2747–2758
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    https://doi.org/10.1021/acs.organomet.6b00517
    Published August 4, 2016
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    An imidazolium salt with a fused benzoferrocenyl was synthesized. This compound was used as an N-heterocyclic carbene (NHC) precursor, and the related ferrocenyl-imidazolylidene complexes Fc-NHC-MLn (MLn = IrCl(COD), IrCl(CO)2, AuCl) were synthesized and fully characterized, including the crystallographic characterization of some of the key structures. The oxidation of the iridium carbonyl compound Fc-NHC-IrCl(CO)2 with acetylferrocenium tetrafluoroborate afforded the oxidized ferrocenium-NHC-IrCl(CO)2 (Fe(III)) species; however the isolated product contained a byproduct resulting from the protonation of the starting Fe(II) complex. The analysis of the electron-donating character of the neutral ligand and the ligand resulting from the oxidation was carried out by studying the variation of the ν(CO) stretching frequencies of Fc-NHC-IrCl(CO)2 and its oxidized analogue, revealing that this shift is 2.9 cm–1, which is consistent with a decrease of the electron-donating character of the ligand produced by the generation of a positively charged metal complex. DFT calculations were carried out in order to rationalize these results. The effects of the oxidation of the ligand in homogeneous catalysis were tested by using a related ferrocenyl-imidazolylidene-gold(I) complex. In the hydroamination of terminal alkynes, the results indicated that the oxidation of the ligand produced a moderate increase of the activity of the gold catalyst. In the cyclization of alkynes with furans, the neutral complex was not active, while the product resulting from its oxidation produced moderate to good yields in the formation of the final products.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.organomet.6b00517.

    • NMR spectra of complexes of the new complexes, cyclic voltammograms of complexes 1, 2, 4, 5, and 7, and computational details, including atomic coordinates of optimized structures (PDF)

    • Crystallographic data for 6-H (CIF)

    • Crystallographic data for 7 (CIF)

    • Crystallographic data for 8-H (CIF)

    • Crystallographic data for 11 (CIF)

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    Organometallics

    Cite this: Organometallics 2016, 35, 16, 2747–2758
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.organomet.6b00517
    Published August 4, 2016
    Copyright © 2016 American Chemical Society
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